The legal nature of EU citizenship remains a hotly debated issue, in particular its relationship with Member State citizenship/nationality. In this paper, we do not explore EU citizenship as such but rather focus on the withdrawal of EU citizenship. To this end, we comparatively analyze the ECJ’s Rottmann ruling and the US Supreme Court’s infamous Dred Scott decision. The paper begins with a critical analysis of the relevant EU case law and literature. In Rottmann, the ECJ, for the first time, had to deal with an inherent tension between the ‘autonomous’ EU legal order and EU citizenship’s ‘dependency’ on Member State nationality. We show that the ECJ took a rather cautious approach, leaving it mainly to the Member States and their courts to determine the ‘appropriateness’ of EU citizenship withdrawal. While the ECJ’s Rottmann approach has been criticized for being too reluctant, we argue that the ECJ – wittingly or unwittingly – was well advised to take such cautious steps with regard to European citizenship. On the basis of an in-depth analysis of Dred Scott v. Sandford we are able to demonstrate some of the challenges of shaping the boundaries of Union Citizenship. The separate opinions delivered in that decision provide an interesting insight into the possible effects of overemphasizing either the dependency or autonomy element of citizenship in multi-level systems. Seen in that light, the ECJ may have been well advised using a cautious, ‘middle-of the-road’ approach. Based on the comparative evidence from Dred Scott, we, however, find that the procedural implementation of the ECJ’s ‘Rottmann test’ lacks bite. As a result, Member States that seek to neglect the autonomous feature of European law can easily use it as a carte blanche. We conclude our paper by proposing a refined ‘Rottmann test’ that avoids Dred Scott-style ‘all or nothing’ excesses and yet can help to strengthen EU citizenship. Under such a refined test, withdrawal of Member State citizenship has to be justified by arguments from European law also, which means that Member States may only withdraw European citizenship when their reasoning is soundly justified also by this standard. Given the lack of primary and secondary law in this respect de lege lata, these minimum legal requirements need to be defined by the ECJ. Unfortunately, in Rottmann, the ECJ missed the opportunity to do so in a coherent way.